26563-68-8

Basic information

• Product Name: (2α,3α)-2,3-Dihydroxy-olean-12-en-28-oic acid
• Synonyms: (2alpha,3alpha)-2,3-Dihydroxy-olean-12-en-28-oic acid;3-Epimaslinic acid;Epimaslinic acid;2,3-Dihydroxy-12-oleanen-28-oic acid
• CAS NO: 26563-68-8
• Molecular Formula: C₃₀H₄₈O₄
• Molecular Weight: 472.70
• Product Categories: Pentacyclic Triterpenes
• Mol File: 26563-68-8.mol
• Article Data: 15

Chemical Properties

• Melting Point: 295-297 °C
• Boiling Point: 570 °C at 760 mmHg
• Flash Point: 312.6 °C
• Appearance: /
• Density: 1.14 g/cm³
• Vapor Pressure: 2.3E-15mmHg at 25°C
• Refractive Index: 1.568
• PKA: 4.63±0.70(Predicted)
• CAS DataBase Reference: (2α,3α)-2,3-Dihydroxy-olean-12-en-28-oic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (2α,3α)-2,3-Dihydroxy-olean-12-en-28-oic acid(26563-68-8)
• EPA Substance Registry System: (2α,3α)-2,3-Dihydroxy-olean-12-en-28-oic acid(26563-68-8)

Safety Data

• Hazardous Substances Data: 26563-68-8(Hazardous Substances Data)

Usage

General Description

"(2α,3α)-2,3-Dihydroxy-olean-12-en-28-oic acid" is a chemical compound which belongs to the class of organic compounds known as triterpenoids. Specifically, it is a pentacyclic triterpenoid and is also considered a derivative of oleanolic acid, consisting of a hydroxyl group at the second and third carbon in the steroid skeleton in addition to a carboxyl group at the 28th position. Due to its complex structure, it is synthesized via multistep organic reactions rather than being present naturally. (2α,3α)-2,3-Dihydroxy-olean-12-en-28-oic acid and its derivatives have been studied for their potential therapeutic uses, including anti-cancer and anti-inflammatory properties. However, more research is needed to fully understand its potential medical applications.

InChI:InChI=1/C30H48O4/c1-25(2)12-14-30(24(33)34)15-13-28(6)18(19(30)16-25)8-9-22-27(5)17-20(31)23(32)26(3,4)21(27)10-11-29(22,28)7/h8,19-23,31-32H,9-17H2,1-7H3,(H,33,34)/t19-,20-,21?,22-,23-,27+,28-,29-,30+/m1/s1

Upstream product

• 108-30-5 succinic acid anhydride 
• 1202006-25-4 2α/β-bromooleanonic acid 
• 73584-62-0 (2α)-2-hydroxy-3-oxo-olean-12-en-28-oic acid 
• 67-64-1 acetone 
• 869788-75-0 (4aS,6aS,6bR,8aR,12aR,12bR,14bS)-10-Acetoxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,12,12a,12b,13,14b-hexadecahydro-2H-picene-4a-carboxylic acid benzyl ester 
• 303114-51-4 oleanolic acid benzyl ester 
• 508-02-1 Oleanolic acid 
• 876723-81-8 2α-hydroxy-3-oxoolean-12-en-28-oic acid benzyl ester 
• 869788-74-9 (4aS,6aS,6bR,12aR)-benzyl 2,2,6a,6b,9,9,12a-heptamethyl-10-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate 
• 464876-77-5 benzyl (2α,3β)-2,3-dihydroxy-olean-12-en-28-oate 
• 106894-29-5 3-acetylmaslinic acid (TARB-2) 
• 6089-92-5 2α,3β-diacetoxyoleane 12-ene-28-carboxylic acid 
• 22425-82-7 methyl maslinate 

Downstream Products

• 1532556-58-3 benzyl (2α,3β)-2,3-di-acetoxy-olean-12-en-28-oate 
• 1575561-28-2 C₄₀H₅₈O₅ 
• 1575561-31-7 C₄₃H₆₂O₆ 
• 1575561-33-9 C₄₁H₆₀O₅ 
• 1575561-37-3 C₄₅H₆₆O₆ 
• 1575561-39-5 C₄₃H₆₄O₅ 
• 1575561-41-9 C₄₉H₇₄O₆ 
• 1575561-44-2 C₄₉H₇₆O₅ 
• 1575561-46-4 C₆₁H₉₈O₆ 
• 1575561-48-6 C₄₄H₅₈O₅ 
• 1575561-53-3 C₅₁H₆₂O₆ 
• 1575561-56-6 C₄₅H₅₈O₇ 
• 1575561-59-9 C₅₃H₆₂O₁₀ 
• 1575561-67-9 C₄₂H₆₀O₇ 

Relevant articles and documents

Synthesis of oxygenated oleanolic and ursolic acid derivatives with anti-inflammatory properties

The scalable syntheses of four oxygenated triterpenes have been implemented to access substantial quantities of maslinic acid, 3-epi-maslinic acid, corosolic acid, and 3-epi-corosolic acid. Semi-syntheses proceed starting from the natural products oleanolic acid and ursolic acid. Proceeding over five steps, each of the four compounds can be synthesized on the gram scale. Divergent diastereoselective reductions of α-hydroxy ketones provided access to the four targeted diol containing compounds from two precursors of the oleanane or ursane lineage. These compounds were subsequently evaluated for their ability to inhibit inflammatory gene expression in a mouse model of chemically induced skin inflammation. All compounds possessed the ability to inhibit the expression of one or more inflammatory genes induced by 12-O-tetradecanoylphorbol-13 acetate in mouse skin, however, three of the compounds, corosolic acid, 3-epi-corosolic acid and maslinic acid were more effective than the others. The availability of gram quantities will allow further testing of these compounds for potential anti-inflammatory activities as well as cancer chemopreventive activity.

Four new triterpenoids isolated from the resin of Garcinia hanburyi

Four new triterpenoids, 2-O-acetyl-3-O-(4′-O-acetyl)-α-l- arabinopyranosylmaslinic acid (1), 2-O-acetyl-3-O-(3′-O-acetyl)-α-l- arabinopyranosylmaslinic acid (2), 2-O-acetyl-3-O-(3′,4′-O-diacetyl) -α-l-arabinopyranosylmaslinic acid (3), and 3-O-(3′-O-acety

Convenient and chromatography-free partial syntheses of maslinic acid and augustic acid

A convenient and chromatography-free 4-step synthesis of analytically pure maslinic acid (1, 41.2%) from oleanolic acid has been developed. Slight variations in the final steps gave an excellent yield of isomeric augustic acid (7, 71.9%).